Bar Hopping
by yes-a-tale
Summary: It was the week before the start of their high school carriers, and what better way to kick it off with a bang? Everyone knows that Chuck always throws a great party. There's a certain hunter prowling the streets after a night of partying on the elite island of Manhattan, and it is only fitting that he ends up at the best fest. Before both shows.
1. Chapter 1: A City Filled With Surprises

Bar Hopping: a Gossip Girl/Supernatural crossover

Summary: It was the week before the start of their high school carriers, and what better way to kick it off with a bang? Everyone knows that Chuck always throws a great party. There's a certain hunter prowling the streets after a night of partying on the elite island of Manhattan, and it is only fitting that he ends up at the best fest. Before both shows.

Parings: Established Nate/Blair

* * *

Chapter One: A City Filled With Surprises

* * *

Dean Winchester felt that this was a satisfying end to a tiring week.

He had been in the New York City metropolitan area for the majority of the past seven days. He stayed in a shady motel (when did he not do so?) in a part of lower Westchester (which was, to his surprise, not as snooty as he thought it was, though he didn't see any of the McMansions), around half an hour outside of the city.

(Staying in the Big Apple would have maxed multiple credit cards and possibly drawn the government's suspicions to him, or to John Smith, or whatever name he had adopted for the time being.)

The tiring commute into the city was done via Metro-North, with their super costly train passes, as driving his _oh so precious _Impala would have been too much of a hassle. No way was he going to let a stranger drive in it in order to park it in a garage. (Not to mention how much he would have to pay.)

Dean didn't trust his ability to find a parking space- the street traffic was very notorious for being terrible 24/7, even worse than its crazy yellow cabs and their foreign cabbies. (A cab, Dean thought, would be a fun thing to take for a spin, albeit an illegal one.)

However, he had soon learned that the pedestrian traffic during rush hours was just as bad. Dean had been pushed multiple times during his coming into the city. Once, some lawyer spilt their coffee on him right as he turned the corner. (Dean didn't even get an apology- all he received was a roll of the eyes! The lawyer or businessman or whatever was a top-notch asshole.)That was not a fun start to the day.

To get to the elephant in the room, Dean was in the city because some snobby Manhattan socialite thought that the foyer of their fifteen-million dollar, posh, new penthouse was haunted by some ghost. She had seen it multiple times, and as a widow living alone with the hired help, it scared her. (Though she had been young for a widow, Dean thought. Then he pondered it for a second longer and glanced at the social climber sitting next to him once again and saw that everything about her was false; from her subtly dyed greying hair, to her breasts, to the lack of movement in her eyebrows which was evidently from trying to get rid of wrinkles, to even her laugh, and so on and so forth.)

She had been right about the haunting. "Of course! I am always right, young man," she had said to him, with an air of smugness and superiority.

The ghost had been her first husband, the one who died from the complications from the hit-and-run accident. Dean assumed that he was concerned about his wife, and how quickly she had moved on.

Her second husband died six months after their marriage. He had been the heir of a big oil company, a trust-fund baby from Texas. (What a gold digger, Dean sneered.) She had two more spouses after the second one- which just furthered Dean's thoughts and opinions.

They both also had sudden, out-of-the-blue deaths, one from cardiac arrest, and the other had had a fatal infection caused by a splinter that was looked over for one too many months.

Dean thought that those facts were suspicious. He could be dealing with a top-class, clean-cut murderer here, but he just pushed that thought to the back of his mind and continued along with his job that he had to complete.

His dad had given him the recommendation to go after this case. They often hunted together, but something popped up in regards to some 'very important matter,' so that's where his dad had to be.

And so now Dean was here, somewhere on the island of Manhattan, following the sounds of the blaring music and the views of the streaming strobe lights and long lines from one club to the next. He had already worked his way through the nearest part of Brooklyn, chatting up an artist or barista or two or maybe twenty. He had gotten laid once already, in the kitchen of some pub that he was pretty sure didn't pass the city's mandated health codes. (He saw a rat- after his escapade, thankfully. It would have been a real mood killer.)

On his way to where he was now, some street in the city, he had stopped at one or two bars. Thank god (or maybe he should thank the devil, since most of the things that he dealt with were the opposite of angelic) that the socialite had been nice and gave him a nice wad of cash in return from his services. (Not _those_ kinds of services, though. He was not, under any circumstances, a gigolo. Dean was a proud manly-man, for heaven's sakes, he _hired _prostitutes, he was not one of them.)

The club right ahead had a line going halfway down the block. Paparazzi were drawn to the entrance like flies, so Dean immediately concluded that this club was one for Manhattan's elite. Like the old socialite's risky friends in their heyday, he mused.

He may have not ever been even more correct.

Since this establishment seemed like one for the record books, Dean hopped onto the line, which was outrageously long.

Well, he was going to, until he was suddenly grabbed. Looking up, he saw that a blonde girl coming out from a taxicab had linked arms with him, and was stumbling her way to the entrance to the club.

Dean wasn't so sure as to what to do in such a situation. Here he was, trying to make sure this woman, this _girl, _didn't face plant onto the pavement. (It would be such a shame, he decided, since she had such a pretty face.)

This task was proving to be a herculean one, as this blonde bombshell in the red over the knee dress could barely stand on her two feet. Dean was trying to stop her and steady the both of them. Her body's momentum, however, decided that Dean was a douche and kept on moving forward, dragging him with it.

Making his way to the door, he noticed that people waiting in line were taking photographs of him and this girl. Dean was surprised to hear the clicks of cameras from phones accompanying the flashes of the paparazzi.

So this mystery girl is somewhat famous? Dean thought that this was the most sensible explanation for the actions he's seen and heard tonight. There were gasps of awe when people saw this Amazonian girl, then the way that some bouncer pointed Dean directly to the door, and the cameras.

The assumption that this girl was extremely popular was Dean's first thought.

His second was that she must be very, very rich.

With her, he made his way to the door and was let through the door with a smile and a nod, along with a motion of where they could check their coats.

Stepping through the entryway, he was invited into the sights, sounds, and smells of the club.


	2. Chapter 2: An Unscheduled Dinner

Bar Hopping: a Gossip Girl/Supernatural crossover

* * *

Chapter Two: An Unscheduled Dinner

* * *

Serena van der Woodsen had an eventful day. To start, it was the first day of school.

If it was just a regular first day, Serena wouldn't have panicked, but it was her first day of high school.

High school! The first day of a new chapter of her life!

She was a little bit nervous, as her high school was all-girls, which meant that she couldn't hang out with Chuck or Nate or her current boy-toy. (The boyfriend of the day, of course, would never be Nate nor would it be Chuck. That was just a preposterous idea, since Nate was Blair's boyfriend. And then Chuck-well, if she needed to elaborate on that to someone, they're obviously new to the Upper East Side. But if she had to say, it was that he was just as big of a whore as she was, so it was never going to happen.)

It did, however, mean major Blair time. The two best friends had a bunch of classes together, which both of them were psyched for. They also took Constance by storm, the blonde superhero and her more manipulative, sneaky sidekick. There were more than a few upperclassmen who cowered in the sight of their new Queens-to-be.

Not one person could say that they were not perfect to rule the courtyard, the marble hallways, the stuffy library, the entirety of Constance.

The queendom was theirs for the taking. It was easy pickings.

Then Gossip Girl, the scandalous informant of the entire adolescent population of the Upper East Side, Manhattan, and possibly the whole city, sent out a blast that for once, Serena was happy about. She was rarely excited about any of the bitch's messages, as Gossip Girl has sent her seemingly okay life spiraling down out of control too many times to count.

"Seven times since her opening this summer," Blair would remind her in a soft sing-song voice, shaking her finger like a parent would do to their three year old who was caught with their hand in the sweets jar. "And," she would continue, "Gossip Girl only sped up the downward descent. You have always been a bit of a mess." Serena would then chuckle, shaking her head in acknowledgement, then correcting Blair, admitting that yes, she's always been a goddamn mess, but she sure is nothing less than a hot one.

The number will eventually go up to eight, Serena knows, when some damaging information that was once a secret is released out into the world via text signed with the dreaded signature of Gossip Girl- "You know you love me, xoxo Gossip Girl."

Serena hated that life-ruining bitch with all of her might, and would most likely kill the blogger if she had a chance.

Anyway, the piece of gold information that was displayed on the screen of her phone was about her and her clique- her elite, filthy rich, gorgeous, fantastic friends. (Serena could think of ways to describe them for days.)

Blair, Nate, Chuck, and Serena were the topics of the blast.

She read it over again, still ecstatic that the gossiping good-for-nothing blogger actually got something right for once.

"Gossip Girl here! It's only lunch, but gossip doesn't have any time restrictions! My blast today isn't too vile, but it'll still rile some people at both Constance and St. Jude's. Watch out royalty, we've got a new dynasty coming to reign. Queens B and S sure shook up the scene this morning. You can see their court part for them in the morning yourselves- thanks gossiplover for the video! St. Jude's had a similar occurrence, and Kings C and N walking around like they owned the place. Well, C was, and N followed. Hopefully the foursome's friendship will stay, and not turn into the _other _type of foursome that you all know that King C and even possibly Queen S would enjoy. Until next time, you know you love me, xoxo, Gossip Girl."

Her life was finally looking up! Even the empress (anything else was too plebian for the life destroyer of many) of scandals said that she's going to be kicking ass and taking names! (Serena could just brush off the crude attempt of a joke at the end of the message. Low blow, Gossip Girl, low blow.)

So Serena kept up her bubbly, happy attitude all through the rest of the school day. She even had a smile on during English, which was not only boring, but it was Serena's most hated subject and she was really bad at it. (Blair could attest to that fact- there were, and still are, many drunk, teary ramblings by Serena about how English was such a stupid class, _"I mean, we already all speak the language, anyway,"_ and the teacher was a bitch.)

However, Serena's smile was taken off of her face when she got home and was greeted by her mom and her mom's new boyfriend. Honestly, her mom, Lily van der Woodsen had _way_ too many boyfriends. She just broke up with one before the summer started, and she must have had a couple of flings on the cruise she went on. (Serena couldn't imagine her mom having one night stands. It was way too _gross_.) But Serena couldn't be sure, since her mom left her and her younger brother, Eric, in the Hamptons to be watched by their grandma, Cece Rhodes.

Oh boy, how that was a _pain _in the ass.

Anyway, Serena didn't think that she could possibly be more upset with her mother, until she was in her room and was told by her ever-adorable brother that there was to be a family dinner tonight. The dinner was going to be an annoyance, since it was with the whole van der Woodsen clan _and_ Lily's new Spanish businessman boyfriend.

"Are you serious?" was Serena's initial reaction upon hearing the news.

Eric nodded, "Yep, orders straight from the dictator. Mom, I mean." He stumbled over the last part, but Serena would have known what he meant. Her mom was extremely demanding for almost never being home.

"Urgh, that is _so_ not cool. You must know-you should know, at least- that Chuck's throwing a huge party to celebrate the start of our high school carriers!" Serena sighed. "Why today, out of all days! Oh my god- like is she s_erious?_"

"I know, I know, Serena. Do you know what? I'll go and ask mom if we can move up the dinner a little bit so that you can still go out and get totally hammered, okay?"

Sometimes, no all the time, Eric was the perfect little brother.

And when Eric promises, Eric comes through. (Most of the time, anyway.) Serena was happy to hear that the dinner was to start at six, not eight like her mom had wanted.

The dinner was much too long for Serena's liking, and therefore nothing really happened. She was much too anxious- Serena had to still pick out her dress to wear later!

The food was delicious, but the dinner conversation was boring.

"How was school?" Her mom would ask.

"Good." Serena rolled her eyes.

"Fine." Eric just looked perpetually bored.

And then Lily would go "Okay," in her concerned-mother voice that both Eric and Serena knew was an act to impress her new, rich Spaniard.

That was repeated for around an hour and a half, in some form or another. Nothing interesting or of upmost importance was said. Serena sighed with relief when she could finally excuse herself, and promptly ran upstairs to her closet.

It was time to start Operation: Find an Outfit.

Serena picked out a red dress that went over her knees. It was lacy, and her mother had shipped it back from London when she stopped there on her cruise. The dress was a McQueen, Serena thinks. She does not have the time to look at the label.

She skips a pair of stockings, as the dress looked great on her still sun-kissed summer skin. The shoes, of course, she couldn't skip, so she found a pair of black Louboutins, easily recognizable by the red soles that matched her dress. As she grabbed a pair of hanging earrings, she decided to pull her hair up into a sleek ponytail.

Grabbing a black double-breasted pea coat and her bag, Serena was out the door and on her way.


End file.
